The Itinerary

A Summer Weekend in the Berkshires

A Summer Weekend in the Berkshires

Yara Akkari's itinerary for a weekend well spent in the Berkshires. Yara is the Founder of Open Spaces Magazine, a publication focused on the intersection of art, travel, and the outdoors. While staying at Life House Berkshires, she curated a guide highlighting local places with the idea in mind that travel– wandering, way finding, discovering–can become something like an art form.


  1. Stop in Great Barrington on the way to Life House for some shopping and a snack at Rubiner's Cheesemongers, followed by an early dinner at Prairie Whale.
  2. Check in at Life House Berkshires, have a night cap in the Library, and get a good night of sleep before a weekend full of exploration.


  1. Wake up within the sunny mountains and grab a coffee and light breakfast at the hotel, then head to the Northern Berkshires. For a nature hike, there are many trails to choose from - we recommend the Mount Greylock Overlook Trail for a moderate level option - it's a 2.4 mile loop with 639ft elevation.
  2. Or, if you prefer a culture-filled day, visit the Clark Art Institute, known for its intimate galleries and stunning natural environment. Make sure to explore the sculpture garden.
  3. The MASS MoCA Museum is another great option for today. It's a contemporary museum in a converted Arnold Prints Works factory building. It's one of the largest visual and performing arts museum in the US.
  4. Check out Mezze, a farm to table restaurant in the nearby Williamstown, for a drink and light bite before driving back to the hotel for dinner at the Club Room.
  5. For an evening performance, check Tanglewood's music schedule. If you are more into dance, check outwhat's showing at Jacob's Pillow, known as "the mecca of dancing," treasured in a 220 acre historic landmark.


  1. Today, focus on the Southern Berkshires for variety. After sipping a cup of coffee or tea at the hotel, grab a to-go picnic from the Club Room and head straight to Olivia's Overlook via Charcoal Trail, a moderately challenging 2 mile loop at 528ft elevation.
  2. Another moderate hike option is the Hickey and Peeskawso Peak Loop, a 2.4 mile hike at Monument Mountain.
  3. For a dose of art before heading back, visit Chesterwood, a historic residence and studio, and one of the earliest venues in the US to showcase large scale contemporary works in an outdoor setting.
  4. If time allows, head to the Norman Rockwell Museum, and then swing by the Red Lion Inn tavern for refreshments in Stockbridge.
  5. Drive back home with many stories and memories of the Berkshires!

More recommendations to fill your time, or for a longer stay:

Restaurants in the Southern Berkshires

  • Prairie Whale: A low key Berkshires outpost, owned by one of the founders of Marlow and Sons in Brooklyn. This rustic spot serves area-sourced American fare and cocktails in a charming house.
  • Rubi's: Tucked away in a cute alley, Rubi's serves natural wine, coffees and an impressive variety of cheese & charcuterie platters and sandwiches, which you can eat right there, by the fireplace. It's the same owner as the next door shop, Rubiner's Cheesemongers.
  • The Old Mill on the Green: An old-school dining room lit by candlelight and a fireplace, surrounded by rolling hills. Takes you back in time.

Restaurants in the Northern Berkshires

  • Mezze: Honest farm to table food inspired by the vast flavors of the Mediterranean and the Berkshires' changing seasons. The restaurant itself has been renovated to be in line with sustainable practices to foster a wholesome and modern ambiance throughout.
  • The Breakroom: Located in Greylock Works, this spot features a menu focused on organic agriculture and local makers.
  • Public Eat + Drink: A busy North Adams pub with local crowds, a wide range of beers, burgers, and grain bowls.

Shops in and Around Lenox

  • The Bookstore: A fixture of the town of Lenox for over 40 years, you can find amazing books, but also get a glass of wine.
  • Haven Cafe & Bakery: Just a 10min drive from Olivia's Overlook, this spot serves breakfast, lunch, and pastries.
  • Shaker Mill Books: Since 2012, the owner of this West Stockbridge bookstore has been selling new, used, and rare books in a local historical landmark. They carry a great selection of photography and art books.
  • N six Depot: A roastery, cafe, and gallery space in West Stockbridge. The owner is a chef and farm owner from Argentina who opened the cafe 12 years ago. Everything is locally sourced.

Shops in Great Barrington

  • Fluff: Sells locally and internationally sourced Alpaca clothes and goods. The owner have an alpaca farm nearby.
  • Farnsworth: A family run cannabis dispensary selling everything from edibles to vintage lighters. The design of the store itself is worth a visit.
  • Familiar Trees: A local bookstore with books on art and design, sold vintage and new.
  • Scout House: A boutique with well curated design, books, furniture, textiles and homeware. Filmmaker Bobby Houston left California to open Scout, while also restoring and flipping historical houses in the area.

Summer Hiking Trails

  • Olivia's Overlook via Charcoal Trail: 2.0 miles, 528 ft elevation, loop, moderate level
  • Hickey and Peeskawso Peak: 2.4 miles, 669 ft elevation, loop, moderate level
  • Race Brook Falls Trail: 3.6 miles, 1230 ft elevation, out & back, moderate level
  • Mount Greylock via Bellows Pipe Trail: 6.5 miles, 2260 ft elevation, out & back, hard level

Historical Houses

  • Frelinghuysen Morris House & Studio: Home of American abstract artists George L.K. Morris and Suzy Frelinghuysen, set on a 46-acre estate in the heart of Lenox.
  • Edith Wharton's Home: Known as The Mount, this country house was the author's home for 10 years. Today it's open to the public with exhibits, concerts, lecture series, and garden light shows.
  • Naumkeag: The former country estate of noted New York City lawyer Joseph Hodges Choate and Caroline Dutcher Sterling Choate. The 44-room mansion is considered an architectural masterpiece.

See Yara on Instagram at @yaraakkari and @openspacesmag.

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